[Journal logo]

Volume 69 
Part 5 
Page o793  
May 2013  

Received 15 April 2013
Accepted 20 April 2013
Online 27 April 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.041
wR = 0.113
Data-to-parameter ratio = 14.5
Details
Open access

4-Formyl-2-nitrophenyl 4-bromobenzoate

aDepartamento de Química - Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia, and bInstituto de Física de São Carlos, IFSC, Universidade de São Paulo, USP, São Carlos, SP, Brazil
Correspondence e-mail: rodimo26@yahoo.es

In the title compound, C14H8BrNO5, the benzene rings form a dihedral angle of 62.90 (7)°. The central ester group is twisted away from the nitro-substituted and bromo-substituted rings by 71.67 (7) and 8.78 (15)°, respectively. The nitro group forms a dihedral angle of 7.77 (16)° with the benzene ring to which it is attached. In the crystal, molecules are linked by weak C-H...O interactions, forming C(12) chains which run along [001]. Halogen-halogen interactions [Br...Br = 3.523 (3) Å] within the chains stabilized by C-H...O interactions are observed.

Related literature

For medicinal and pharmaceutical properties of nitroaromatic compounds, see: Jefford & Zaslona (1985[Jefford, C. W. & Zaslona, A. (1985). Tetrahedron Lett. 26, 6035-6038.]); Bhattacharya et al. (2006[Bhattacharya, A., Purohi t, V. C., Suarez, V., Tichkule, R., Parmer, G. & Rinaldi, F. (2006). Tetrahedron Lett. 47, 1861-1864.]); Benedini et al. (1995[Benedini, F., Bertolini, G., Cereda, R., Dona, G., Gromo, G., Levi, S., Mizrahi, J. & Sala, A. (1995). J. Med. Chem. 38, 130-136.]); For similar structures, see: Moreno-Fuquen et al. (2011[Moreno-Fuquen, R., Ellena, J. & De Simone, C. A. (2011). Acta Cryst. E67, o2869.], 2013[Moreno-Fuquen, R., Mosquera, F., Ellena, J., Tenorio, J. C. & De Simone, C. A. (2013). Acta Cryst. E69, o570.]); Moreno-Fuquen (2011[Moreno-Fuquen, R. (2011). Acta Cryst. E67, o3114.]). For van der Waals radii, see: Bondi (1964[Bondi, A. (1964). J. Phys. Chem. 68, 441-452.]). For halogen-halogen interactions see Awwadi et al. (2006[Awwadi, F. F., Willett, R. D., Peterson, K. A. & Twamley, B. (2006). Chem. Eur. J. 12, 8952-8960.]); Hathwar et al. (2010[Hathwar, V. R., Roopan, S. M., Subashini, R., Khan, F. N. & Guru Row, T. N. (2010). J. Chem. Sci. 122, 677-685.]). For hydrogen bonding, see: Etter (1990[Etter, M. (1990). Acc. Chem. Res. 23, 120-126.]); Nardelli (1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).

[Scheme 1]

Experimental

Crystal data
  • C14H8BrNO5

  • Mr = 350.12

  • Monoclinic, P 21 /c

  • a = 6.5308 (2) Å

  • b = 8.2253 (2) Å

  • c = 25.6860 (8) Å

  • [beta] = 103.1910 (9)°

  • V = 1343.38 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.08 mm-1

  • T = 295 K

  • 0.38 × 0.16 × 0.12 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.568, Tmax = 0.687

  • 16446 measured reflections

  • 2746 independent reflections

  • 2095 reflections with I > 2[sigma](I)

  • Rint = 0.086

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.113

  • S = 1.03

  • 2746 reflections

  • 190 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C13-H13...O1i 0.96 2.37 3.254 (4) 153
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5309 ).


Acknowledgements

RMF is grateful to the Spanish Research Council (CSIC) for the use of a free-of-charge licence to the Cambridge Structural Database. RMF also thanks the Universidad del Valle, Colombia, for partial financial support.

References

Awwadi, F. F., Willett, R. D., Peterson, K. A. & Twamley, B. (2006). Chem. Eur. J. 12, 8952-8960.  [CrossRef] [PubMed] [ChemPort]
Benedini, F., Bertolini, G., Cereda, R., Dona, G., Gromo, G., Levi, S., Mizrahi, J. & Sala, A. (1995). J. Med. Chem. 38, 130-136.  [CrossRef] [ChemPort] [PubMed]
Bhattacharya, A., Purohi t, V. C., Suarez, V., Tichkule, R., Parmer, G. & Rinaldi, F. (2006). Tetrahedron Lett. 47, 1861-1864.  [CrossRef] [ChemPort]
Bondi, A. (1964). J. Phys. Chem. 68, 441-452.  [ISI] [CrossRef] [ChemPort]
Etter, M. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hathwar, V. R., Roopan, S. M., Subashini, R., Khan, F. N. & Guru Row, T. N. (2010). J. Chem. Sci. 122, 677-685.  [CSD] [CrossRef] [ChemPort]
Jefford, C. W. & Zaslona, A. (1985). Tetrahedron Lett. 26, 6035-6038.  [CrossRef] [ChemPort] [ISI]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Moreno-Fuquen, R. (2011). Acta Cryst. E67, o3114.  [CSD] [CrossRef] [details]
Moreno-Fuquen, R., Ellena, J. & De Simone, C. A. (2011). Acta Cryst. E67, o2869.  [CSD] [CrossRef] [details]
Moreno-Fuquen, R., Mosquera, F., Ellena, J., Tenorio, J. C. & De Simone, C. A. (2013). Acta Cryst. E69, o570.  [CrossRef] [details]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o793  [ doi:10.1107/S1600536813010830 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.